


Guilty Feelings

by wittywhitly



Category: Prodigal Son (TV 2019)
Genre: Excessive Drinking, F/M, Post-Episode: s01e11 Alone Time, Sex, Slow Burn, Smut
Language: English
Status: Completed
Published: 2020-02-10
Updated: 2020-02-10
Packaged: 2021-02-27 21:15:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 4,823
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22652371
Author URL: https://archiveofourown.org/users/wittywhitly/pseuds/wittywhitly
Summary: After Malcolm's failure to go on vacation, Jessica seeks Gil's help.
Relationships: Gil Arroyo & Jessica Whitly
Kudos: 21





	1. A Mother's Love

Jessica watches the rain cascade down the windows of her beautiful home, while she sips upon a rather strong martini. Its been a rough few days of trying to convince Malcolm he still needs to take a break – she even enlisted Ilsa in an attempt to force him onto the plane. It didn’t work. She loves her son dearly but he refuses to think about his health which forces her to do the thinking for him. _Constantly_. She worries every day about him, as he continues to obsess over murder and his father’s actions. Why can’t he see that she’s only trying to help?!

Ainsley stopped by a couple of times to check in on her. Ainsley has always been more understanding and easier to manage. She was too young to remember her father before he was imprisoned. Other than that reckless interview; she’s been angelic to raise. In this family Ainsley cares for Jessica, Jessica cares for Malcolm and Malcolm hopelessly cares for his parakeet. On her last visit, Ainsley called Jessica a hypocrite - Jessica frets over the wellbeing of Malcolm to the point it jeopardizes her own health _and_ social life. Over the years Ainsley has made numerous attempts at relieving her mother’s worries. No amount of spa visits or lavish dinner parties ever took Jessica’s mind off of Malcolm. The life guru she hired for Jessica’s 50th birthday did not go down well; she scoffed and scolded him so much that after 1 week, he quit and moved out of state. Ainsley has even set her mother up with countless men, New York’s finest bachelors but her mother has never shown up for a single date. The problem is that Jessica doesn’t believe she should be happy. How could Jessica deserve happiness when she let Martin kill all those women right under her nose? Of course, she didn’t know but how could she not have figured it out and stopped him? That duty then fell upon her 10-year-old son whom now is scarred beyond repair.

It’s 5pm. Jessica emerges from her bedroom for the 1st time today. She’s had long enough to wallow in self-pity – plus she’s out of vodka. She’s showered, dressed and ready to scorn anyone in her path. She’s off to visit an old friend. An old friend with a lot of influence.


	2. One Drink

**Summary for the Chapter:**

> Gil agrees to go for a drink with Jessica to clear the air.

Gil sits at his desk reading Edrisa’s notes on a recent victim’s autopsy. It was a gruesome murder – every torture technique in the book had been used before the victim’s life was ended by an overdose on Tylenol. The perpetrator was clearly unhinged and wanted to inflict as much pain as possible. Out of the corner of his eye, he could see Bright engrossed in his work. Bright was in his element. Gil is always conflicted when he brings him onto a case. Bright thrives on murder and he’ll always catch the killer but each case has a lasting impact on his mental health. Gil is fearful that sooner or later, Bright will crack.

Gil tosses the file onto his desk and lets out a sigh. His office is stuffy and the turtle neck he’s wearing isn’t helping. Time for some fresh air to clear his thoughts. It was a tip Jackie gave him. She used to say that whenever your mind is cluttered, a walk in the park will always make the noise go away and provide clarity. He runs his hands through his hair, as he walks over to the door, grabbing his jacket on the way.

After letting the team know he’s headed out, Gil makes his way to the exit. He steps outside and feels the cold New York wind hit his rough skin. He closes his eyes and breathes in the crisp air. Just then, he hears a car pull up. He opens his eyes to see a familiar black Mercedes. The windows are tinted and there is a chauffeur in the driver’s seat. She’s here. Adolpho steps out of the car and spritely opens the passenger door. A pair of black Jimmy Choo’s appear on the pavement, as Jessica Whitly emerges.

“Aaah! Gil! Just the man I was looking for,” she said as she stepped towards him. “You look like you could use a drink and honestly, so could I. I mean who am I kidding, when could I not use a drink?”

Gil looks at her confused as to why she’s come all the way here. She looks gorgeous of course. Her hair is perfectly curled. She’s wearing a tight maroon dress which hugs her curves magnificently. He assumes it was custom made - the Whitlys don’t just buy off the rack. Her cream Burberry trench coat is loose and fluttering in the wind.

“I was just headed out to clear my head, things can get pretty heavy in my line of work. Sometimes it’s good to just take a walk.” He doesn’t feel like chatting, not after reading what happened to that poor victim.

“Walking is… good… if you’re happy to step in dog shit and god knows what else. A drink makes everything better and you can do it indoors… out of the cold… and away from dog shit.” She senses his hesitance. Things have been a little tense since Jessica involved the press with the girl in the box situation.

Gil looks around at the bustling streets, as he toys with the idea. He looks into Jessica’s eyes. She looks sad. Like she hasn’t been sleeping well. He can see that her intentions are good and that she clearly wants to speak to him. Maybe she wants to make amends for the media storm she created. Maybe she wants to talk about Malcolm. Whatever it is, it seems important.

“One drink,” he says sternly holding up his finger, as though he wasn’t clear enough. “I have work to do and booze is never truly the answer Jess. It’s a temporary fix.”

His concern is sweet but a little harsh in tone. Jessica smiles and pivots back towards the car. Adolpho opens the door and Jessica and Gil climb inside. They remain silent for the entire journey.


	3. A Whole Lot of History

**Summary for the Chapter:**

> Gil and Jessica have been through a lot since Martin's arrest.

Where to begin with Gil and Jessica. So much water under the bridge. Their relationship has been fraught for so many years. They don’t communicate well. Mainly because they’re both afraid to say what they really mean. 2 decades of suppressed emotions have been bubbling underneath the surface. Neither one understands the other. And they’re both so stubborn that they rarely make a breakthrough. The last few months, however, have been smooth for them. They’ve not been so close in years. All of that was squandered when Jessica called every newspaper and network in the city.

When Martin was taken away, it wasn’t just Malcolm he felt he had a duty to take care of. Jessica was so vulnerable and yet had to be so strong for her two children. Gil would pick Malcolm up from school and bring him back to his home in Brooklyn, where Jackie would have dinner on the table waiting. After dinner, Gil would help Malcolm with his homework before driving him back to the upper east side. Gil would arrive and tell Malcolm to head to his room so that he could check on Jessica. She would be functioning but visibly drunk. No one can function so highly a bottle of brandy deep quite like Jessica Whitly. Gil would sit with her, have her drink water and eat. He’d try to console her and tell her that things would get better. She hated herself as much as Martin. The routine repeated every night for a couple of years. Gil watched Jessica slowly get back on her feet. He cared for her and desperately wanted to see her happy. Occasionally they’d argue about how to help Malcolm through his many issues but for the most part, it was a strong and admirable friendship. Anyone could see they had a close bond. Some may have said too close. Something changed though. Suddenly their friendship ended. The routine changed. Gil would drop Malcolm off outside the Whitly house and drive away. Gil and Jessica avoided seeing and speaking to each other at all costs. No one is entirely sure what happened.

Nowadays, Gil and Jessica have laid down their swords and are practically co-parenting Malcolm once again.

Adolpho parks the car and assists Gil and Jessica out of the car. Jessica walks proudly towards the front door. Gil is stationary. He’s still hesitant about having a drink with Jessica. Why couldn’t they just have had a chat in his office? He shrugs off his doubts. He knows Jessica hates that place and that she probably didn’t want Malcolm around. He joins her as they head inside.


	4. Co-parenting

**Summary for the Chapter:**

> Gil and Jessica workout their issues for the sake of Malcolm.

A maid hurries into the drawing-room with fresh supplies of booze. Gil expects that to be a daily occurrence with the amount Jessica knocks back. He can’t help but worry about her. She would definitely benefit from a trip to rehab but she’d never go. She’s far too proud.

Beer is usually Gil’s drink of choice, nothing better than kicking back with a cool bud and watching Law and Order. Gil loves that show, well loves to laugh at all the inaccuracies. Cop shows never get it right. He watches as Jessica whips up to whiskey sours and sashays her way over to the spot on the sofa next to him. He catches a whiff of her perfume. A luxurious scent. He’s not sure of the brand but he knows it’ll be something obnoxiously overpriced. Doesn’t matter though, she smells amazing.

“Cheers!” Jessica raises her glass before taking a large gulp of the liquor. Jessica knows she has an unhealthy relationship with alcohol… and pills… and her children. She justifies it because it’s all that has kept her going for the last 20 years. She couldn’t be the formidable woman she is today without a drink in her hand.

“So what’s all this about? Are you going to explain away the bracelet fiasco?” Gil barks, as he slowly sips on his drink. Jessica knows how to make a good cocktail; he’ll give her that.

“Gil. I’ve apologized for the uncomfortable position it put you in but I didn’t know what else to do. And my team and I are making real progress. Who knows, we might have a breakthrough any day now.” She wills him to move past this. It’s been incredible having him back in her life as a friend and confidant. Gil always knows what to say to calm Jessica. His support means everything to her.

Gil says nothing. He places his glass on a nearby coaster, he’s not impressed with her response.

“Anyway…” Jessica places her glass down and shuffles in her seat as she approaches the real reason, she wanted to speak with him. “That isn’t what this is about. I wanted to talk to you about Malcolm. He didn’t take that mandatory vacation that you were meant to enforce. He _needs_ a break, Gil. You know that his mental health is on thin ice.”

Gil ponders on her words. He wants to stay angry but at the end of the day, Jessica is just a caring mother looking out for her troubled son. Besides, Gil has also been fretting about Malcolm and his refusal to go on leave.

“Jess, I know Malcolm. I know when he’s spiralling and at the moment, I genuinely believe he’s ok. I agree he should have taken his leave but right now, the best place for him is in the field. It takes his mind off of things and we can keep an eye on him. And this isn’t just me speaking as his boss who marvels at his work. I would never put work above his wellbeing. I care too much about him and you to let that happen. You have my word that as soon as I start to see him crack, he’s out of there.”

“Gil, I just-” Jessica tries to plead with him. He takes hold of her hands and brings them to her lap.

“Jess, you can trust me. What happened with John Watkins scared the hell out of me too. I didn’t think he could come back from that. He almost lost you and Ainsley. He almost lost his life… it’s a miracle he didn’t lose his mind. But I’m telling you, he is safe and I am watching.”

Jessica sighs. She wants to fight back but she can see it’s no good. His mind is made up.

“Ok. Ok, he can stay _for now_. Thank you for looking out for him. You’ve always been there for him. The best surrogate father anyone could ask for.”

Gil lets out a small grin before Martin’s words fill his mind. His grip on her hands loosens.

“Something the matter?” Jessica can see the change on Gil’s face. She senses she triggered him. Is this because he’s not actually a father? He and Jackie couldn’t have children. Oh, no has she put her foot in her mouth?

“It’s nothing. It’s just something Martin said when-”

“ _MARTIN_?! Don’t let that man get inside your head. What on earth did he say to you?” Jessica is horrified that once again, Martin is coming between her and someone she cares about.

“Nothing. I mean… ugh, he just commented on my _role_ in this family.” He pauses, reaches for his glass and takes a swig. “He said that I am trying to replace him.”

“Well for goodness sake is that not a positive? Replacing him. Erasing him. You’re the best thing to ever happen to Malcolm.”

“But I didn’t _try_ to. It was organic. Authentic.” Gil takes another sip. Martin’s words really stayed with him. “It’s not just that. He inferred that I wasn’t just trying to replace him as Malcolm’s father.” Gil took another sip, this time much larger.

Jessica looks baffled. “I’m sorry, I’m not following. God Martin lives for this. Getting inside your mind. Malcolm’s mind. My mind. He is a master manipulator. Gil, please, what did he say? It’s obviously affected you. Your whole demeaner has changed.”

“You’re right, I shouldn’t let him get to me. I know that he wants me to distance myself. He knows that making me seem like a snake is the worst thing anyone could say to me.”

Jessica prompts him to continue. She’s eager to heat what games Martin has been playing.

Gil takes a deep breath. Repeating what he said. Saying it out loud. It’s difficult. It almost gives it some truth. “He suggested that I was- that there was something going on between us. That we were… involved. He said that I am not worthy of a woman like you. That you must pity me and hate him.”

There it is. He said it. He can’t take it back now, though he fears it will change their relationship forever. He looks at her longing to see her response.

Jessica is stunned. She turns towards the coffee table, covering her mouth with her hands in disbelief. She shakes her head as the words sink in. Gil places a comforting hand upon her knee.

“I just can’t believe he’d stoop _so_ low,” she says in a deep tone. “No wonder you were spooked and aloof. He really got to you.” She turns back towards him and focuses on his eyes. “Gil, I’m sorry he said that and made you feel so small. You’re a good man. He would say anything to lash out at you because you were there for me and this family after he destroyed us. He can’t stand that. He can’t stand that another man was able to take care of us and that he can’t control us anymore.”

Gil rubs her knee before removing it and moving in for a hug. They engage in a meaningful embrace. Gil is used to being the one with the consoling words. It’s new for Jessica to be the supportive one. The one doing the healing. Turns out she’s actually pretty good at it. He breathes in as they hold each other. God, she smells even better up close. They part and turn back to their empty glasses.

Jessica smiles and asks, “Well. Whatta you say, how about another?”

Gil hides a smile. “Got any beer?”

“Afraid not. My bar is well stocked but beer is just a little too um… classless. How about a chardonnay?”

Gil chuckles and shakes his head. Typical Jessica. “Sure, chardonnay it is.”


	5. One Too Many

**Summary for the Chapter:**

> Tipsy talks between old friends.

The atmosphere in the drawing-room has become very merry over the last 4 hours – well it was bound to after 3 bottles of wine and countless cocktails later. Jessica and Gil entered into a cocktail competition at one point. Jessica merged a Long Island Iced Tea with a Manhattan and called it an Upper East Side. Gil made some concoction with Kahlua, chili, and coconut milk and named it the Manila Heat. The coffee table can no longer be seen under the dozens of photo albums and poorly balanced empty glasses. Jessica and Gil really needed to let off some steam.

“God I can’t believe I’m about to say this but I think we may have had too much to drink.” Jessica bursts into laughter immediately after finishing her sentence. She can handle her drink but even she has pushed it a little too far. She is laid on the sofa balancing a spoon on her nose.

Gil laughs along and says, “you’re probably right. I didn’t know how much I needed this. To let go and just have fun. I don’t remember the last time I laughed so much. It’s been years since I’ve had this much fun.” Gil stands up from the floor and heads to the bar to pour 2 glasses of water.

“I’m glad I could remind you to live a little every once in a while. Although, I think we are both guilty of taking life too seriously.” Gil hands her the water. She reaches out, sits up and moves her legs over to make room for Gil.

Gil sits beside her nodding, as he drinks his water. “With everything we have going on, you can’t blame us for being so tightly wound. We both need to get out more and enjoy life.”

Jessica tilts her head to face Gil. “Easier said than done my friend. It sure would be a lot easier to enjoy life if there was someone to share those moments with. Unfortunately, I’m pretty isolated – partly my choice and partly due to Martin. I’ve lost count of how many friends abandoned me as soon as they heard about everything. You’d think I was the murderer. I am a social pariah. Ainsley has attempted to help me in my isolation from society but… I don’t know I feel like how can I enjoy my life, date, have friends and so on if my son is suffering?” She sits up and stairs down into her glass.

Gil moves along the sofa and puts one arm around her. “Jessica, you’re no good to anybody if you’re not ok. Malcolm needs you, needs us to be strong to help him. And if we’re not happy, we’re not strong. It’s taken me a long time to realize that and I’m guilty of not adhering to it.” Jessica rests her head on Gil’s shoulder. They sit drinking their water for a few moments. They are silent but comfortable. Just being in each other’s company is enough. They were taking in the night and the words shared. Tonight has taught them they may be alive but they’re not living and that needs to change.

“Thank you. For that. That advice is so true. And thank you for everything you’ve done for me and my family. I don’t know where we’d be without you. Truly.” She said softly while looking up at him. “Maybe we should do more together. Set aside some time every now and again to have fun. To stop things getting too much. To be there for each other because no one else is. I can’t burden my children with my issues, I need a real friend.”

Gil felt that fuzzy feeling again. It comes occasionally when he and Jessica are together. When they’re real with each other and cut the crap, he finds himself in a state. His heart races and he gets flustered. He knows what it means but he always suppresses it. When he and Jessica first became close, he had the feeling constantly. When they fell out, he put up walls to stop him thinking about her. Since they’ve reconnected, the feeling has increased in frequency and he can’t help but think it won’t stop this time. He was always faithful to Jackie and never admitted to himself how he truly felt about Jessica. He always wanted more but hated himself for having that desire. The night they fell out was the night he let his feelings come to light. He and Jessica kissed. Only briefly. But it happened. And he had to stop seeing her because Gil is a loyal man and could never hurt Jackie. It’s been 3 years since Jackie passed away. It’s killing Gil not to act on his feelings but how could he move on from Jackie. It still feels like a betrayal even if she is dead.

Gil finds himself placing a hand on Jessica’s cheek. She leans in closer as their lips meet. Her lips are soft and plush. His goatee is bristly and is tough on her skin. The kiss gradually increases in pressure. They pause. Both staring at one another’s lips not knowing whether to stop or live in the moment. Both frantically trying to decide how to proceed. Gil moves his hand from Jessica’s cheek. He’s not sure what to do with it but before he can decide, she takes his hand and places it on her waist and pulls him in for another kiss. This kiss is stronger, more passionate. Her tongue finds a way into his mouth. This kiss is breathy and long but still tangled in mixed emotions.

Gil pulls away and looks at Jessica. He looks her up and down like he’s making calculations. Trying to figure out what is going on, what he’s feeling. Jessica looks longingly back at him. Her heart is wildly racing. Unlike Gil, she was unaware that her feelings had crept back and have been growing ever since Malcolm joined the NYPD.

Gil throws himself into their third kiss, this time committing to what is to follow. He places both his hands on her cheek as she leans down onto the sofa. He’s on top of her as they kiss deeply. She tastes like vodka and her cherry lip gloss. He tastes like whiskey and cologne. The years have passed but it feels like no time has gone by since they shared their last kiss almost 20 years ago. Gil pauses as he stands to allow the disrobing to begin and he ushers Jessica to do the same. They embrace in another kiss as he puts his arms around her to begin unzipping her dress. He moves his hands down her back slowly, savoring every moment. Once the dress is unzipped, he takes the opportunity to caress her lush ass and pull her in even closer. She shimmies out of the dress and it falls to the floor. He stands back to take all of her in. She’s wearing a plunging black lace bra that perfectly cups her bulging breasts. Jessica has had 2 children but her body doesn’t show it. Her panties are of course matching and lucky for Gil, she’s wearing a thong. She still has on her fierce Jimmy Choo’s – Gil can’t understand how she lasts so long wearing such uncomfortable shoes. Jessica puts her hands out and feels for Gil’s belt buckle and pull him towards her body. She can feel his erection rubbing against her throbbing thighs. Once his belt is unbuckled, she swiftly removes his pants, while he removes his turtle neck.

Gil pauses to awkwardly take off his shoes and socks. Jessica lets out a little laugh. He returns to her and squeezes her ass again. Their bodies writhing up and down in harmony. Neither of them has had sex for years but this was flowing so naturally for them. Gil’s erection was intense. He felt 25 again. He rubbed his hard dick on her clit. His boxers dampened as she’d already soaked her thong through. They were both ready. Gil lifted his hands slightly to tuck them under her thong. He pulled her thong to the floor and knelt down in synchrony. He was at the perfect spot to suckle on her pulsating clit. Jessica let out a gasp as he began licking between her thighs. Gil was giving martin a run for his money with the moves he had. She felt so alive. Gil dug his tongue into her pussy. His right hand rubbing her clit, his left fingering her ass. She was in ecstasy. Her legs were quivering as she came again and again. Maybe she should have taken off the heels. She continued to bite her lip but her groans were still loud and Gil knew his magic was working. He finally came up for air and began to work his way up her body. He kissed his way across her hips, licked up her abdomen, paused to remove her bra and bite on her nipples. He finally returned to kiss her lips and she threw her legs and arms around him. He was carrying her.

She kicked off her heels as she whispered in his ear, “the countertop.” He followed instructions and took her to the bar. She chewed upon his neck and ear the whole time. His weak spot. At this point, Gil was already so close to finishing but he wanted to savor every moment in her arms. Jessica shuffled forward on the marble countertop to push down his boxes. His thick dick pounced out and she quickly took hold. Gil groaned her name. He was responding extremely well to her touch. Jessica knows how to work a man’s body. She repaid the favor and popped a finger in his ass too. Gil’s eye widened. He’d never experienced this before and it was pushing him over the edge. He took charge of the situation. He brought her closer and pushed his dick between her dripping thighs and into her pussy. It was warm and sensational. The countertop wasn’t the most comfortable place for Jessica to be grinding on but the cold marble was incredible against her bare skin. Gil didn’t last long after the ass fingering but he lasted long enough to make her orgasm one last time. Her legs gripped around his body and toes curled as they both climaxed.

They were so out of breath. Both in disbelief at what had just happened but equally so happy it did. They stayed at the countertop with their heads touching as the panted. Finally, Gil stepped back and ran his fingers through his hair. He was in awe at her hot, sweaty naked body. Jessica through her head back and laughed.

“Well. That was- who knew how much we needed that.”

Gil smirked as he offered her a hand down from the counter. They collected their clothes and redressed. Gil sat down on the sofa to finish his water. Jessica shortly joined him. They didn’t know what to say. How to address what just happened. They couldn’t process it.

“We shouldn’t tell Malcolm about this,” Gil said trying to regain his sensibility.

“Damn, I was just about to call him to tell him all about my 1st orgasm in 20 years.” She chuckled. “We won’t tell anyone till we know what it was. And I guess we won’t know what it was until we talk about it. God, I sound like my therapist.” She scoffed taking another sip. “We may even have to do it again to fully understand,” Jessica was laughing at her own joke to break the tension. She could tell Gil wasn’t dealing with it well.

Gil turned to her with a smile. His emotions were scattered across the room and his face showed it. His crippling guilt wouldn’t allow him to be happy. “Good idea. It stays between us. I should get going but we can talk about it you know sometime. I just need a while to deal with it… alone… first.”

Jessica was even more confused by that comment. She didn’t understand the full extent of what Gil was feeling. “Ok. Well um, you know where I am when you’re ready to… talk.”

Gil stood up, put one hand on her shoulder as a goodbye and left. Jessica replaced the water with gin.


End file.
